Water → 5-(3,4-Dichlorophenyl)-5-[2-[4-phenyl-1-azoniabicyclo[2.2.2]oct-1-yl]ethyl]-3-[3,5-bis(trifluoromethyl)benzyl]tetrahydro-2H-1,3-oxazin-2-one chloride

HRID 1601907Notes

Reaction equation

HRID 1601907 reaction equation
[C:1]1([C:7]23[CH2:14][CH2:13][N:10]([CH2:11][CH2:12]2)[CH2:9][CH2:8]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:15][C:16]([F:51])([F:50])[C:17]1[CH:18]=[C:19]([CH:43]=[C:44]([C:46]([F:49])([F:48])[F:47])[CH:45]=1)[CH2:20][N:21]1[CH2:26][C:25]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[C:36]([Cl:41])[CH:35]=2)([CH2:27][CH2:28]OS(C)(=O)=O)[CH2:24][O:23][C:22]1=[O:42].O.CCOCC>CN(C=O)C>[Cl-:40].[Cl:41][C:36]1[CH:35]=[C:34]([C:25]2([CH2:27][CH2:28][N+:10]34[CH2:13][CH2:14][C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)([CH2:8][CH2:9]3)[CH2:12][CH2:11]4)[CH2:24][O:23][C:22](=[O:42])[N:21]([CH2:20][C:19]3[CH:18]=[C:17]([C:16]([F:51])([F:50])[F:15])[CH:45]=[C:44]([C:46]([F:49])([F:47])[F:48])[CH:43]=3)[CH2:26]2)[CH:39]=[CH:38][C:37]=1[Cl:40]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 1428104-Phenyl-1-azabicyclo(2.2.2)octaneHCID 158866773-[3,5-Bis(trifluoromethyl)benzyl]-5-(3,4-dichlorophenyl)-5-[2-(methanesulfonyloxy)ethyl]tetrahydro-2H-1,3-oxazin-2-one

Product 1

HCID 195913605-(3,4-Dichlorophenyl)-5-[2-[4-phenyl-1-azoniabicyclo[2.2.2]oct-1-yl]ethyl]-3-[3,5-bis(trifluoromethyl)benzyl]tetrahydro-2H-1,3-oxazin-2-one chlorideYield 24.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.53 g of 4-phenyl-1-azabicyclo[2.2.2]octane and 1.4 g of the compound obtained in step C of EXAMPLE 4 in 5 ml of DMF is heated at 60° C. for 5 hours. After cooling to RT, the reaction mixture is poured into water and extracted with DCM, the organic phase is washed twice with 2 N HCl solution and three times with saturated NaCl solution and dried over MgSO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using DCM and then a DCM/MeOH mixture (92/8; v/v) as the eluent. The product obtained is taken up with ether and the precipitate formed is wrung to give 0.21 g of the expected product. M.p.=138° C.

Workup

  1. temperatureAfter cooling to RT
  2. extractionextracted with DCM
  3. washthe organic phase is washed twice with 2 N HCl solution and three times with saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. customthe solvent is evaporated off under vacuum
  6. customThe residue is chromatographed on silica
  7. customThe product obtained
  8. customthe precipitate formed

Sources & evidence

ORD record
ord-81ea9da5f6e145a885d991ef3b35d1dc
Source dataset
uspto-grants-1999_11
Patent number
US05977359

Reaction notes

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